m-Chloroperbenzoic acid → Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxide

HRID 266123ノート

反応式

HRID 266123 の反応式
[Cl:1][CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N:4]=1.ClC1C=CC=C(C(OO)=[O:40])C=1>CO>[Cl:1][CH2:2][C:3]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:10]2[C:5](=[CH:6][C:7]([O:30][CH3:31])=[C:8]([O:28][CH3:29])[CH:9]=2)[N+:4]=1[O-:40]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

生成物 1

HCID 21851158Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxide収率 65%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate (3.0 g), m-chloroperbenzoic acid (85%, 2.3 g) and methanol (40 ml) was stirred under reflux for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (6:4, v/v) gave ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate 1-oxide (2.0 g, 65%). This was recrystallized from acetone-isopropyl ether. Colorless prisms, mp. 193°-194° C.

後処理

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-ethyl acetate (6:4, v/v)

出典と根拠

ORDレコード
ord-866c1e4d32984556835cd359f3e03c0c
出典データセット
uspto-grants-1997_07
特許番号
US05650410

反応ノート

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